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I can relate to what you are going through. You use your canned stuff to get your foot in the door, then you try to freestyle a little just to keep the ball rolling. Then you try to neg or say something sarcastic/funny and it just kind of falls flat and then the walls goes up and they blow you out. Also sounds like you are trying too hard. Try to give less of a fuck. You need to not come across as outcome-dependent. Meaning, don't make it seem like you are desperately trying to look cool and hit on them with a bunch of clever dialogue in the hopes of getting a number.
Another thing, you are probably falling into the trap of saying something or asking a question like "Guess where I"m from?" Then trying to milk the suspense or make it funny. Regardless of whether you succeed in that or if they say "don't know" and let the steam out of your sail, it ends up being anti-clamactic. I think you are dwelling on each line hoping to get all you can from it. What you need to do is be eager to get to the next thing, acting like the last thing you or she said really didn't matter. That will keep your energy up and keep them guessing and prevent them from losing interest as you stammer and stall and go quiet.
Wow in terms of what I am doing that is pretty much is spot on. Thanks